Red disazo dye.



' rivative thereof. The new disazo dyestuffs.

UNITED STAT "PATENT oEEIoE.

WILHELM BAUER, or VOHWTINKEL, NEAR ELBERFELD, GERMANYY A'SSIGNOR TO 'FARBENFABRIKEN VQRM. FRIEDR. BAYER & 00.,

0F ELBERFELD, GERMANY, A CORPORATION OF GERMANY.

I R'ED DISAZO DYE.

0- till whom it may concern:

Be it known that I, W1LHELM BAUER, doctor of philosophy,-'chemist, a citizen-of the erman Empire, residing at'Vohwin'kel, near by the combination of one molecule of the tetrazo compoundof para-para-diaminodiphenylether of hydroquinon of the formula nent of which at least one is the .gl ami'no-5- naphthol-7-sulfonic acid or a substituted depossess good affinity for the vegetable fiber. They dye unmordanted cotton bright-red shades fast to acids,

The process for the production of these dyestuffs consists in combining one molecule' of tetrazotized para-para-diaminodiphenylether of hydroquinon. of the abovev given formula either withtwo molecules of 2-amino-5-naphthol-7-sulfonic acid or sub.- stituted derivatives thereof or with one molecule of one of these compounds and one molecule of any other-suitable con' ponent, or

vice vers'a. V I

The new dyestuffs correspond to the general formula 1 I wherein stands for an a'zodye stufi component, such as a naphthol-sulfonic acid, ami- Specification of Letters Patent. Application filed July 13, 1906. Serial hlS invention relates to the-preparation- 10 of new-tetrazo dyestuffs centrated sulfuric a1nino-5-naphthol-7-sulfonic acid.

PatentedvDec .25, 1906. No. 326.117.

stands for hydrogen, alkyl, acidyl,or aryLsuch as acetyl, OH COOH,) benzoyl, phenyl, toly-l, or the-like. They are in' the shape of their alkaline salts dark powders soluble in water with a red color, dyeing unmordanted cotton red shades and'yielding upon reduction with stannous chlorid and hydrochloric acid para-para-diaminodiphenylether of hydroquinon.

The para para diamino diphenylether of hydroquinon, unknown till now, is obtained by treating salts of hydroquin'one. 9., the

, potassiumsalt-withpara-nitrohalogen-benzenee. g.,- para-nitrochlorobenzene-and subsequent reduction of the resulting dinitro compound. The alcohol in the shape of colorless needles, melting at'170 centigrade. It is soluble in hot alcohol, ether, and benzene.- Its H01 salt forms long colorless needles easily solublev in water. They are precipitated again from the aqueous solution by the addition of concentrated hydrochloric acid.

The invention is illustrated by the follow-v ing e ramples, the parts being by weight: Jxample I: Two hundred and ninety-four arts of para-para-diaminodiphen'ylether of lydroquinon are diazotized in the usual manner by means of one hundred and forty parts of sodium nitrite. and the necessary quantity of hydrochloric acid. The result ing tetrazo compound is then added test well- 'cooled solution of four hundred and eighty parts of 2-amino-5naphthol-7sulfonic acid, sufl'icient sodium carbon,- ate has been added to maintain the whole alkaline. The formation of the dyestuif is complete after some hours. precipitated during the preparation is filtered ofl 'anddried. It is after being dried and ulverizcd a dark powder having a metallic liiste'r soluble in water with a red and in con acid witha violet color and 'yielding'up'on reduction with stannons chlorid and hydrochloric acid para-para-diaminodiphenylether of hydroquinon and di- It dyes unmordanted cotton scarlet-red shades fast to acids. The dye-baths are nearly exhaustto which solution .edafter dyeing. The process-is-carried out in an analogous manner on replacing the 2- new body crystallizes from v The dyestufi a:nino5 -naphthol-7-sulfonic acid with the substituted derivatives of this acid, such as Z-acetylaiuino-5-naphthol-7-sulfonic acid or the like.

Example 11: Two hundred and ninetyfour parts of para-para-diaminodiphenyb ether of hydroquinon are dia zotized in the usual manner by means of one hundred and forty parts of sodium nitrite. Two hundred and iorty-seven parts of the sodium salt of 2- naphthol-7-sulfonic acid dissolved in water with an excess of sodium carbonate are added to the well-cooled tetrazo compound. After the formation of the intermediate compound is complete a solution of two hundred and thirty-nine parts of 2-amin05-na,.'hthol7- suifonic acid is added, and the mixture of the reaction is stirred until the formation of the d-i'sazo dyestufl' is complete. The dyestuli thus obtained dyes unmordanted cotton red shades.

The 2-naphthol-7-sulfonic acid can be replaced by the substituted derivatives of 2- amino-5-naphthol-7sulfonic acid or by any other component suitable for the preparation of azo dyestufis.

Dycstufl' f m para-para-diamiriodiphenyldycs unmordantem. r of hydroquinone+ ed cotton 1. 2m0l.0 UniDOlllLPllthOl-7-Sllli0l1l 5 acid} scarlet 2. lmol.of2.5-aininonaphthol-T-sulionic acid 1 scarlet (acid solution) +1 mol. of 2.5-aniinonaphth01-7-suliimic acid (alkaline solution) 1 mol. oI l-naphthol-4-sulfonic acid-+1 mol. oi 2z5-aminonapnthol-T-sulfonic acid 1 incl. of 2-naphthol-T-sulionic ueid+l moi. of 2.fi-aminoiiaphthol-T-sullonic acid 1 mol. of .kphenylamine -naphtholT-sul Ionic acid-H inel. of 2.5-aininonapntliol- 7-sulionic acid mol. of. 2.5-:1ininoiiaphthol-T-sullonic acid 1 moi. of 2.5-dioxynaphtlmlene-7- SUlfOniii acid mol. 0i 2lLC(t'lziIIliHO-i-Ihl[)litl1()l-LiSllll'on'ic acid- -l moi. of 2.5-aminonaphthei- 7-sulfonic avid 101. of z'flcCtyllUnlIlO-fi-HZIPllllhOl-T'Sllllonicncid-i-l moi. oi 2-n mino-5-mmhthol- 7-sulionic acid mel. el 2.5-:l1mmmuphthol-T-sullonic acid l moi. of the glyehi ol LS-aminonapl'lthol-Fsullonir neid moi. of 2.5-:unin nphthol-7-suli'enic acid 1 mol. of 2.5muiinomiphlhol-LT- disulioni acid mo]. of lacetylamine-S-mphthol-ii-sulionic acid linol. of 'J-phenylamino5- iiaplitlioi-7-sulfonic acid mol. of .Uraminounphthol-T-sulfonic aeid+l mol. of 5.5-diuXy2.2-dinuphthylamin-U-disullon' ne'ul 11:01. of Z-awlylmnino -u;i htnol-ii-snl mm amid 1 mo]. 1' the izlyi'in o[ 2.5- nmnioimpliih :l-T-sulh llll :u'iil yellowish red red red

sea rlet red scarlet red bluish red Having now des ibed my invention and 11 what mariner the same is to be performed,

what I claim as new, and desire to secure by Letters Patent, is

1. The herein-described new tetrazo dyestuffs of the general formula:

t \N k a 5 a son! 1 wherein Y stands-for an .azo-dyestuif conglonent and X for hydrogen, aryl, alkyl, aei yl, which in the shape oftheir alkaline salts are dark powders soluble in water with a red color; dyeing unmorda-nted cotton red shades; and yielding upon reduction with stannous chlorid and hydrochloric acid para-paradiaminodiphenylether of h *dro uinon, substantially as hereinbefore escribed.

2. The herein-described new tetrazo'dyestuff of the formula:

so .,n n whielrin' the shape of its sodium salt is adark powder having a metallic luster soluble in water with. a red and in concentratedsulfuric acid with a violet color; dyeing immordanted cotton scarlet-red shades; and yieldin upon reduction with stannous chlo'nid *and' hydrochloric acid para-parasdiaminodiphcnylether of hydroquinon and :diamino-S-axephthoLY- sulfonic acid, substantially as -l1ereinbefero described.

In testimony'wh'ereof I :have hereunto set my hand in the presence of two subscribing witnesses.

WILHEIJM BAUER.

Witnesses O'r'ro KoNIe, J. A. RITTERSHAUS. 

